Patent GB-1428296-A (GB)
Title: Silver halide colour photographic materials
IPC: C09B53/00
Filed: 1974-03-27
Abstract: 1428296 # - (2,4 - Di - tert - amylphenoxy)- ethanol and butanol and their derivatives FUJI PHOTO FILM CO Ltd 27 March 1974 [27 March 1973] 13677/74 Heading C2C [Also in Division G2] # - (2,4 - Di - tert - amylphenoxy) - ethanol is prepared by reducing 2,4-di-tert-amylphenoxyacetic acid chloride in anhydrous diethyl ether with LiAlH 4 . # - (2,4 - Di - tert - amylphenoxy)- butanol is prepared similarly. 5-[#-(2,4-Di-tertamylphenoxy) - ethoxycarbonyl] - 2 - chloroaniline is prepared by heating to 130-140 C. methyl 3-amino-4-chlorobenzoate and 2,4-ditert-amylphenoxyethanol using tetrabutyl titanate as an ester exchange catalyst. 5-[#-(2,4- di - tert - amylphenoxy) - butoxy - carbonyl] - 2- chloroaniline is prepared similarly. 5<SP>1</SP> - [#- (2,4 - di - tert - amylphenoxy) - ethoxycarbonyl]- (2<SP>1</SP> - chloro) - benzoylacetanilide is prepared by heating to 120-130 C. for 3 hours at reduced pressure ethyl-benzoylacetate and 5-[#-(2,4-ditert - amylphenoxy) - ethoxycarbonyl] - 2- chloroaniline. 5<SP>1</SP> - [# - (2,4 - Di - tert - amylphenoxy) - ethoxycarbonyl] - (2<SP>1</SP>- chloro) - 2 - methyl - benoxylacetanilide, 5<SP>1 </SP>- [# - (2,4 - ditert - amyl - phenoxy) - butoxycarbonyl] - (2<SP>1</SP> - chloro) - benzoylacetanilide, and 5<SP>1</SP> - [# - (2,4- di - tert - amylphenoxy) - butoxycarbonyl] - 2<SP>1</SP>- chloro - α - (2 - methylbenzoyl) - acetanilide are prepared similarly. 51 - [# - (2,4 - Di - tertamylphenoxy) - ethoxycarbonyl] - 2<SP>1</SP>- chloro - α- bromo - α - (2 - methyl - benzoyl) - acetanilide is prepared by adding bromine dropwise to 5<SP>1</SP>- [# - (2,4 - di - tert - amylphenoxy) - ethoxycarbonyl] - 2<SP>1</SP> - chloro - α - (2 - methylbenzoyl)- acetanilide in chloroform. 5<SP>1</SP>-[#-(2,4-Di-tertamylphenoxy) - ethoxycarbonyl] - 2<SP>1</SP> - chloro - α- phthalimido - α - (2 - methylbenzoyl) - acetanilide is prepared by stirring the last prepared compound and potassium phthalimide in dimethylformamide for 5 hours at 23 C. 5<SP>1</SP>-[#-(2,4-Ditert - amylphenoxy) - ethoxycarbonyl] - 2<SP>1</SP> - chloro- α - (5,5 - dimethyl - 3 - hydantoinyl) - α - (2- methylbenzoyl) - acetanilide and 5<SP>1</SP> - [# - (2,4- di - tert - amylphenoxy) - ethoxycarbonyl] 2<SP>1</SP>- chloro - α - (5,5 - dimethyl - 2,4 - dioxo - 3 - oxazolidinyl) - α - (2 - methylbenzoyl) - acetanilide are prepared similarly. 1 - (2,4,6 - Trichlorophenyl)- 3 - (2 - chloro - 5 - methoxycarbonylanilino)- 2-pyrazol-5-one is prepared by stirring for 5 hours at 130-140 C. #,#-diethoxyacrylic acid ethyl ester and 2-chloro-5-methoxycarbonylaniline to give #-ethoxy-#-(2-chloro-5-methoxycarbonylanilino)acrylic acid ethyl ester (not isolated) and refluxing for 2 hours with 2,4,6- trichlorophenylhydrazine and glacial acetic acid. 1 - (2,4,6 - Trichlorophenyl) - 3 - {2 - chloro - 5- [# - (2,4 - di - tert - amylphenoxy) - ethoxycarbonyl] - anilino} - 2 - pyrazol - 5 - one is prepared by reacting the last prepared compound with #-(2,4-di-tert-amylphenoxy)-ethanol using tetrabutyl titanate as an ester exchange catalyst. 1 - Hydroxy - 2 - {5<SP>1</SP> - [# - (2,4 - ditert - amylphenoxy) - ethoxycarbonyl] - 2<SP>1</SP> - chloro}- naphthanilide is prepared by heating 1-hydroxy- 2-naphthoic acid phenyl ester with 3-amino-]- [# - (2,4 - di - tert - amylphenoxy) - ethoxycarbonyl] - 4 - chlorobenzene for 1 hour at 150-160 C. and while keeping the system at reduced pressure at the same temperature and distilling off the phenol formed, continuing the reaction for 2 hours.